SYNTHESIS AND DIELS-ALDER REACTIONS OF (+)-(S)-1-TERT-BUTYLSULFONYL-1-PARA-TOLYLSULFINYLETHENE, A NEW MASKED CHIRAL KETENE EQUIVALENT

被引:38
作者
LOPEZ, R [1 ]
CARRETERO, JC [1 ]
机构
[1] UNIV AUTONOMA MADRID,FAC CIENCIAS,DEPT QUIM CI,E-28049 MADRID,SPAIN
关键词
D O I
10.1016/S0957-4166(00)80525-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Enantiomerically pure (+)-(S)s-1-t-butylsulfonyl-1-p-tolysulfinylethene (1) was easily prepared in three steps from t-butyl methyl sulfone. The catalyzed Diels-Alder reactions of 1 with cyclopentadiene were highly stereoselective. The major adduct was transformed into (+)-(1R,4R)-dehydronorcamphor and (+)-(1R,4S)-2-t-butylsulfonyl-2,5-norbornadiene.
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页码:93 / 96
页数:4
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